# US 10,308,636 B2 · Aromatic heterocyclic compound

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- Number: US 10,308,636 B2
- Document ID: US10308636B2
- Status: Granted
- Kind: B2
- Application number: 15/250,379
- Filed: 2016-08-29
- Published: 2017-02-23
- Granted: 2019-06-04
- Earliest claimed: 2012-06-15
- Assignees: Mitsubishi Tanabe Pharma Corporation
- Applicants: Mitsubishi Tanabe Pharma Corporation
- Inventors: Kunio Saruta; Norimitsu Hayashi; Osamu Sakurai; Hiroaki Sawamoto; Eri Ooboki
- Web page: https://patentgrep.com/patent/US10308636B2

## CPC

- C07D 401/14: containing three or more hetero rings
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/06: Antihyperlipidemics
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 9/12: Antihypertensives
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 27/02: Ophthalmic agents
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D 249/14: Nitrogen atoms
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/10: linked by a carbon chain containing aromatic rings
- C07D 405/14: containing three or more hetero rings
- C07D 409/14: containing three or more hetero rings
- C07D 413/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The compound represented by the general formula: wherein ring A is benzene which may be substituted and the like; ring B is benzene which may be substituted and the like; X is a single bond and the like; Y is alkyl which may be substituted and the like; Z is CR1 or nitrogen atom; R1 is hydrogen and the like; R2 is alkyl which may be substituted and the like or a pharmaceutically acceptable salt thereof is useful as a prevention/treatment agent of obesity, diabetes, and the like.

## Claims

### Claim 1

A compound represented by the general formula (1-A):
[wherein ring A is pyridine which may be substituted with 1 to 3 alkyl groups;
ring B1 is benzene which may be substituted with 1 to 3 substituent groups which are each independently alkyl, halogen or cyano;
R1 is hydrogen, halogen atom, alkoxy, or alkyl which may be substituted with 1 to 6 halogen atoms;
R2a is the formula as below:
{wherein Z′ represents a single bond, alkylene, -Alk-O—, or -Alk1-O-Alk2-, (wherein Alk, Alk1, and Alk2 each independently represent alkylene, and the bond at the right end represents a bond to ring C),
ring C represents an aromatic hydrocarbon group,
R3 and R4 each independently represent hydrogen, halogen atom, alkyl which may be substituted with 1 to 6 halogen atoms, or alkoxy which may be substituted with alkoxy or 1 to 6 halogens atoms};
X is a single bond or —O—;
Ya is alkyl which may be substituted with 1 to 3 substituent groups which are aminocarbonyl which may be substituted with alkyl which may be substituted with 1 to 3 hydroxy and carboxy, or cycloalkyl which may be substituted with 1 to 3 carboxyalkyl groups];
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein X is —O—; and Ya is alkyl substituted with carboxy, or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

The compound according to claim 1 which is selected from
2,2-dimethyl-3-({4-methyl-5-[3-methyl-4-(5-phenyl-1H-imidazol-2-yl)phenyl]pyridin-2-yl}oxy)propanoic acid,
2,2-dimethyl-3-({5-[3methyl-4-(5-phenyl-1H-imidazol-2-yl)phenyl]pyridin-2-yl}oxy)-propanoic acid,
2,2-dimethyl-3-({5-[4-(5-phenyl-1H-imidazol-2-yl)phenyl]pyridin-2-yl}oxy)-propanoic acid
3-[(5-{4-[5-(4-methoxyphenyl)- 1H-imidazol-2-yl]phenyl}pyridin-2-yl)oxy]-2,2-dimethylpropanoic acid,
3-[(5-{3-cyano-4- [4-(4-methoxyphenyl)-1H-imidazol-2-yl]phenyl}-4-methylpyridin-2-yl)oxy]-2,2-dimethylpropanoic acid,
2,2-dimethyl-3-({4-methyl-5-[4-(5-phenyl-1H-imidazol-2-yl)phenyl]pyridin-2-yl}oxy)-propanoic acid, and
3-[(5-{4-[5-(4-methoxyphenyl)-1H-imidazol-2-yl]phenyl}-4-methylpyridin-2-yl)oxy]-2,2dimethylpropanoic acid,
or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 1)

A pharmaceutical composition comprising the compound according to claim 1 or a pharmaceutically acceptable salt thereof as active ingredient and a pharmaceutically acceptable carrier.